I started with an internet startup company in 1997. They paid out a small amount of stock options — which grew exponentially in value over the years, especially with splits. I hung in there for five years, allowing my options to fully vest. They were worth several hundred thousand when I left to take a less stressful job.

If I had simply hung on to my full portfolio, without touching it, I could retire today. E-company is massive. Instead, I sold a bunch to reinvest in retirement funds — not a BAD idea, but it has grown a fraction of the stock value. And every time I felt it peaked, causing me to sell some, it took off again, making my sell-off a constantly bad idea.

Now I have to sell some every year to stay “retired” while working other jobs — it’ll probably be gone when my retirement fund kicks in. If I had left it alone and trusted in its growth I would be living like a king now for the rest of my life. None of my other investments paid off.

It’s a reminder, if nothing else, that there are many, many ways we can screw up financially — even if we think we’re doing the right thing at the time.

If you’ve been following the series, what’s your favorite essay and/or podcast?